A series of novel amphiphiles were synthesized based entirely on renewable resources. Besides their efficacy as supramolecular gelators in a wide variety of organic solvents and also water, their surface properties as surfactants and emulsifiers have been determined. A methodical study revealed that the length of the hydrocarbon chains has a dramatic and decisive influence on the thermal stabilities of the obtained hydrogels.
A library of novel, lipid-modified derivatives of ascorbic acid was shown to exhibit highly attractive properties as surfactants, emulsifiers, oil soluble antioxidants, and highly effective gelators in organic solvents and especially water. In these systems, intermolecular hydrogen bonding and van der Waals forces act synergistically to induce gelation as confirmed by spectroscopic studies. The morphology of the formed gel has been characterized by scanning electron microscopy.
The lack of fatty aldehyde dehydrogenase function in Sjögren Larsson Syndrome
(SLS) patient cells not only impairs the conversion of fatty aldehydes into their
corresponding fatty acid but also has an effect on connected pathways. Alteration of
the lipid profile in these cells is thought to be responsible for severe symptoms
such as ichtyosis, mental retardation, and spasticity. Here we present a novel
approach to examine fatty aldehyde metabolism in a time-dependent manner by measuring
pyrene-labeled fatty aldehyde, fatty alcohol, fatty acid, and alkylglycerol in the
culture medium of living cells using HPLC separation and fluorescence detection. Our
results show that in fibroblasts from SLS patients, fatty aldehyde is not
accumulating but is converted readily into fatty alcohol. In control cells, in
contrast, exclusively the corresponding fatty acid is formed. SLS patient cells did
not display a hypersensitivity toward hexadecanal or hexadecanol, but 3-fold lower
concentrations of the fatty alcohol than the corresponding fatty aldehyde were needed
to induce toxicity in SLS patient and in control cells.
The reaction of hydroxycarboxylic acids, such as citric, malic and tartaric species with an excess of fatty acid chlorides produces the corresponding O-acylated hydroxycarboxylic anhydrides in one step and in a near quantitative yield. These molecules are excellent electrophiles which react readily with a variety of nucleophiles including alcohols, diols and polyols. Their reaction with triethylene glycol and triethylene glycol monomethyl ether leads to two series of novel anionic surfactants, which are unsymmetrical gemini surfactants. The determination of their properties (CMC, foaming, HLB) revealed that these molecules are-depending on the chain length of the fatty acid-excellent emulsifiers, and that they also display interesting antimicrobial activity. These novel functional surfactants are of interest for applications in food and personal care products and for the formulation of pharmaceuticals.
Die Reaktion von 1,′,3,3′‐Tetrakis(dimethylamino)‐1λ5, 3λ5 ‐diphosphet (1) mit Schwefelwasserstoff führt zu Bis(dimethylamino)thiophosphonylmethyliden‐methyl‐bis(dimethylamino)phosphoran(5). Wasser spaltet aus 5 Dimethylamin ab und bildet Bis(dimethylamino)thiophosphonyl‐methyl(dimethylamino)phosphonylmethylen 6. Bei der Umsetzung von 1 mit Ethylmercaptan entstehen das 2,4‐Bis(ethylthio)‐Derivat von 1, die Verbindung 8 und Bis(dimethylamino)‐phosphanylmethyliden‐methyl‐bis(dimethylamino)phosphoran (9), das auch aus 1 und 2, 4, 6‐Trimethylphenyl‐phosphan gebildet wird. Thiophenol protoniert 1 zum entsprechenden Kation, das als Thiophenolat 10 isoliert wird. Eigenschaften, NMR‐ und Massenspektren von 5, 6 und 8 – 10 werden beschrieben und diskutiert.
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